Methyl iodide → HCID 13235936, compound

HRID 1169434Notes

Reaction equation

HRID 1169434 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7]CC)=[O:6].Cl[CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[C:15]1([CH2:14][O:1][C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=2)[C:5]([OH:7])=[O:6])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 68451-ChloromethylnaphthaleneHCID 11430Potassium CarbonateHCID 24522Ethyl 3-hydroxybenzoate

Product 1

HCID 13235936HCID 13235936, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture comprising ethyl 3-hydroxybenzoate (5.00 g), 1-(chloromethyl)naphthalene (5.40 ml), potassium carbonate (6.24 g), methyl iodide (a catalytic amount) and acetone (50 ml) was heated at reflux for 24 hours. After the reaction mixture was concentrated under reduced pressure to remove the solvent, the residue was mixed with water (200 ml) and was extracted with ethyl acetate. After the organic layer was concentrated, a 1 N aqueous solution of sodium hydroxide (50 ml) was added to the residue dissolved in methanol (50 ml), and the resulting mixture was heated at reflux for 2 hours. After being cooled to room temperature, the reaction mixture was acidified by the addition of concentrated hydrochloric acid and was then extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride, was dried with anhydrous sodium sulfate and was then evaporated under reduced pressure to remove the solvent. The resulting residue was recrystallized from ethyl acetate/hexane to obtain 3-(1-naphthylmethoxy)benzoic acid (7.14 g) as colorless crystals.

Workup

  1. temperatureat reflux for 24 hours
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure
  3. customto remove the solvent
  4. additionthe residue was mixed with water (200 ml)
  5. extractionwas extracted with ethyl acetate
  6. concentrationAfter the organic layer was concentrated
  7. additiona 1 N aqueous solution of sodium hydroxide (50 ml) was added to the residue
  8. dissolutiondissolved in methanol (50 ml)
  9. temperaturethe resulting mixture was heated
  10. temperatureat reflux for 2 hours
  11. additionthe reaction mixture was acidified by the addition of concentrated hydrochloric acid
  12. extractionwas then extracted with ethyl acetate
  13. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  14. dry with materialwas dried with anhydrous sodium sulfate
  15. customwas then evaporated under reduced pressure
  16. customto remove the solvent
  17. customThe resulting residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4d26931e7c574c3796c6d30ac2823ab1
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

Loading…